2-{(3S,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahydro-4-methylidenefuran-3-yl}-1H-isoindol-1,3(2H)-dione

Base Information

• Chemical Name: 2-{(3S,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahydro-4-methylidenefuran-3-yl}-1H-isoindol-1,3(2H)-dione
• CAS No.: 292864-88-1
• Molecular Formula: C₃₀H₃₁NO₄Si
• Molecular Weight: 497.666

Synonyms:2-{(3S,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahydro-4-methylidenefuran-3-yl}-1H-isoindol-1,3(2H)-dione

Chemical Property of 2-{(3S,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahydro-4-methylidenefuran-3-yl}-1H-isoindol-1,3(2H)-dione

Chemical Property:

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Technology Process of 2-{(3S,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahydro-4-methylidenefuran-3-yl}-1H-isoindol-1,3(2H)-dione

There total 7 articles about 2-{(3S,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahydro-4-methylidenefuran-3-yl}-1H-isoindol-1,3(2H)-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 51.0%

potassium phtalimide (1074-82-4) + Methanesulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl ester (292864-87-0) → 2-{(3S,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahydro-4-methylidenefuran-3-yl}-1H-isoindol-1,3(2H)-dione (292864-88-1)

Guidance literature:

In N,N-dimethyl-formamide; at 110 ℃;

DOI:10.1002/1522-2675(20000705)83:7<1398::AID-HLCA1398>3.0.CO;2-I

Reference yield:

1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose (20590-54-9) → 2-{(3S,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahydro-4-methylidenefuran-3-yl}-1H-isoindol-1,3(2H)-dione (292864-88-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / NaH / dimethylsulfoxide / 0.5 h / 20 °C

2: 78 percent / HCl; water / methanol; dioxane / 2 h / Heating

3: 78 percent / Me₃SiCl; hexamethyldisilazane / 17 h / Heating

4: 84 percent / pyridine

5: 83 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

6: 51 percent / dimethylformamide / 110 °C

With pyridine; hydrogenchloride; chloro-trimethyl-silane; water; sodium hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrolysis / 3: demethoxylation / 4: silylation / 5: mesylation / 6: Substitution;

DOI:10.1002/1522-2675(20000705)83:7<1398::AID-HLCA1398>3.0.CO;2-I

Reference yield:

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (20590-53-8) → 2-{(3S,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahydro-4-methylidenefuran-3-yl}-1H-isoindol-1,3(2H)-dione (292864-88-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 67 percent / P₂O₅ / dimethylsulfoxide / 20 h / 30 °C

2: 89 percent / NaH / dimethylsulfoxide / 0.5 h / 20 °C

3: 78 percent / HCl; water / methanol; dioxane / 2 h / Heating

4: 78 percent / Me₃SiCl; hexamethyldisilazane / 17 h / Heating

5: 84 percent / pyridine

6: 83 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

7: 51 percent / dimethylformamide / 110 °C

With pyridine; hydrogenchloride; chloro-trimethyl-silane; water; phosphorus pentoxide; sodium hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Oxidation / 2: Condensation / 3: Hydrolysis / 4: demethoxylation / 5: silylation / 6: mesylation / 7: Substitution;

DOI:10.1002/1522-2675(20000705)83:7<1398::AID-HLCA1398>3.0.CO;2-I

upstream raw materials:

potassium phtalimide

Methanesulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl ester

1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

Downstream raw materials:

(3S,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahydro-4-methylidenefuran-3-amine

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